# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Sergiy Rosokha' 'Bing Han.' 'J Kochi' 'Jianjiang Lu.' _publ_contact_author_name 'Sergiy Rosokha' _publ_contact_author_email SROSOKHA@UH.EDU _publ_section_title ; Unusual Structural Effects of Intermolecular pi-Bonding in the Tetracyanopyrazine (Ion-Radical) Dimer ; # Attachment 'TCP-AnionRad.cif' data_TCP_K_Crown _database_code_depnum_ccdc_archive 'CCDC 703968' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H52 K O8, C8 N6' _chemical_formula_sum 'C36 H52 K N6 O8' _chemical_formula_weight 735.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.743(3) _cell_length_b 10.035(3) _cell_length_c 11.123(3) _cell_angle_alpha 81.707(5) _cell_angle_beta 69.085(5) _cell_angle_gamma 73.712(5) _cell_volume 973.8(4) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 53 _cell_measurement_theta_min 4.29 _cell_measurement_theta_max 18.58 _exptl_crystal_description brick _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 393 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.955 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14720 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 30.03 _reflns_number_total 5609 _reflns_number_gt 3497 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.630 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5609 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1308 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.59407(16) -0.09340(15) 0.91586(13) 0.0418(3) Uani 1 1 d . . . C2 C 0.62678(15) 0.03144(15) 0.92026(13) 0.0400(3) Uani 1 1 d . . . C3 C 0.69841(18) -0.19184(17) 0.82294(16) 0.0527(4) Uani 1 1 d . . . C4 C 0.76473(17) 0.06152(15) 0.83354(16) 0.0470(4) Uani 1 1 d . . . N1 N 0.46655(14) -0.13045(13) 0.99493(12) 0.0459(3) Uani 1 1 d . . . N3 N 0.78183(18) -0.26945(18) 0.74835(17) 0.0778(5) Uani 1 1 d . . . N4 N 0.87606(17) 0.08434(15) 0.76435(15) 0.0638(4) Uani 1 1 d . . . K1 K 0.5000 0.5000 0.5000 0.04704(15) Uani 1 2 d S . . O1 O 0.75971(11) 0.32285(10) 0.32014(9) 0.0440(3) Uani 1 1 d . . . O2 O 0.73686(10) 0.34895(11) 0.58133(9) 0.0440(3) Uani 1 1 d . A . O3 O 0.50089(11) 0.54312(10) 0.73389(8) 0.0434(3) Uani 1 1 d . A . C10 C 0.84166(17) 0.22368(17) 0.39090(14) 0.0503(4) Uani 1 1 d . . . H10A H 0.9379 0.1711 0.3309 0.060 Uiso 1 1 calc R A . H10B H 0.7812 0.1569 0.4401 0.060 Uiso 1 1 calc R . . C11 C 0.87416(16) 0.29645(17) 0.48056(13) 0.0490(4) Uani 1 1 d . A . H11A H 0.9479 0.2312 0.5173 0.059 Uiso 1 1 calc R . . H11B H 0.9191 0.3740 0.4336 0.059 Uiso 1 1 calc R . . C12 C 0.75967(16) 0.42167(16) 0.67008(13) 0.0424(3) Uani 1 1 d . . . H12A H 0.7892 0.5079 0.6276 0.051 Uiso 1 1 calc R A . H12B H 0.8421 0.3632 0.7008 0.051 Uiso 1 1 calc R . . C13 C 0.61578(16) 0.45645(16) 0.78111(13) 0.0418(3) Uani 1 1 d . A . H13A H 0.5859 0.3703 0.8235 0.050 Uiso 1 1 calc R . . H13B H 0.6301 0.5054 0.8453 0.050 Uiso 1 1 calc R . . C14 C 0.37123(16) 0.61607(15) 0.83104(12) 0.0409(3) Uani 1 1 d . . . H14A H 0.4079 0.6555 0.8881 0.049 Uiso 1 1 calc R A . C15 C 0.28730(17) 0.73670(16) 0.76406(14) 0.0445(3) Uani 1 1 d . . . H15A H 0.3572 0.7961 0.7122 0.053 Uiso 1 1 calc R . . C16 C 0.15347(19) 0.82236(18) 0.86652(15) 0.0554(4) Uani 1 1 d . . . H16A H 0.1922 0.8621 0.9207 0.067 Uiso 1 1 calc R A . H16B H 0.0971 0.9005 0.8237 0.067 Uiso 1 1 calc R . . C17 C 0.04834(18) 0.7381(2) 0.95004(15) 0.0619(5) Uani 1 1 d . A . H17A H 0.0019 0.7054 0.8975 0.074 Uiso 1 1 calc R . . H17B H -0.0341 0.7966 1.0172 0.074 Uiso 1 1 calc R . . C18 C 0.13217(19) 0.6133(2) 1.01402(15) 0.0618(5) Uani 1 1 d . . . H18A H 0.0621 0.5544 1.0629 0.074 Uiso 1 1 calc R A . H18B H 0.1665 0.6461 1.0756 0.074 Uiso 1 1 calc R . . C19 C 0.26942(18) 0.52692(17) 0.91394(14) 0.0499(4) Uani 1 1 d . A . H19A H 0.3266 0.4515 0.9584 0.060 Uiso 1 1 calc R . . H19B H 0.2343 0.4838 0.8593 0.060 Uiso 1 1 calc R . . O21 O 0.5503(4) 0.7814(6) 0.4491(3) 0.0776(13) Uani 0.570(8) 1 d P A 1 C21 C 0.6958(9) 0.7910(8) 0.4446(6) 0.0802(19) Uani 0.570(8) 1 d P A 1 H21A H 0.7386 0.7160 0.4991 0.096 Uiso 0.570(8) 1 calc PR A 1 H21B H 0.6903 0.8822 0.4726 0.096 Uiso 0.570(8) 1 calc PR A 1 C22 C 0.7869(4) 0.7744(8) 0.3051(4) 0.0834(18) Uani 0.570(8) 1 d P A 1 H22A H 0.8314 0.6750 0.2863 0.100 Uiso 0.570(8) 1 calc PR A 1 H22B H 0.8695 0.8228 0.2789 0.100 Uiso 0.570(8) 1 calc PR A 1 C23 C 0.6736(5) 0.8400(6) 0.2368(4) 0.0567(12) Uani 0.570(8) 1 d P A 1 H23A H 0.6894 0.9309 0.1946 0.068 Uiso 0.570(8) 1 calc PR A 1 H23B H 0.6820 0.7788 0.1708 0.068 Uiso 0.570(8) 1 calc PR A 1 C24 C 0.5244(7) 0.8574(8) 0.3404(6) 0.077(2) Uani 0.570(8) 1 d P A 1 H24A H 0.4787 0.9568 0.3588 0.093 Uiso 0.570(8) 1 calc PR A 1 H24B H 0.4544 0.8221 0.3144 0.093 Uiso 0.570(8) 1 calc PR A 1 O31 O 0.6192(12) 0.7032(7) 0.4001(10) 0.125(3) Uani 0.430(8) 1 d P A 2 C31 C 0.7370(14) 0.7275(11) 0.4092(11) 0.099(3) Uani 0.430(8) 1 d P A 2 H31A H 0.8294 0.6605 0.3596 0.119 Uiso 0.430(8) 1 calc PR A 2 H31B H 0.7318 0.7178 0.5005 0.119 Uiso 0.430(8) 1 calc PR A 2 C32 C 0.7424(10) 0.8748(9) 0.3558(11) 0.103(3) Uani 0.430(8) 1 d P A 2 H32A H 0.7097 0.9392 0.4260 0.124 Uiso 0.430(8) 1 calc PR A 2 H32B H 0.8456 0.8787 0.2979 0.124 Uiso 0.430(8) 1 calc PR A 2 C33 C 0.6351(13) 0.9078(10) 0.2848(13) 0.116(4) Uani 0.430(8) 1 d P A 2 H33A H 0.5565 0.9940 0.3159 0.140 Uiso 0.430(8) 1 calc PR A 2 H33B H 0.6889 0.9227 0.1918 0.140 Uiso 0.430(8) 1 calc PR A 2 C34 C 0.5694(14) 0.7996(10) 0.3040(11) 0.092(4) Uani 0.430(8) 1 d P A 2 H34A H 0.6009 0.7529 0.2224 0.110 Uiso 0.430(8) 1 calc PR A 2 H34B H 0.4575 0.8336 0.3349 0.110 Uiso 0.430(8) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0364(7) 0.0459(9) 0.0414(8) -0.0022(6) -0.0155(6) -0.0044(6) C2 0.0337(7) 0.0441(8) 0.0410(7) 0.0014(6) -0.0151(6) -0.0059(6) C3 0.0440(9) 0.0562(10) 0.0571(10) -0.0120(8) -0.0112(8) -0.0142(8) C4 0.0395(8) 0.0410(8) 0.0548(9) 0.0017(7) -0.0161(7) -0.0026(6) N1 0.0395(7) 0.0459(7) 0.0508(7) -0.0045(6) -0.0147(6) -0.0077(5) N3 0.0589(10) 0.0811(11) 0.0851(11) -0.0381(10) 0.0002(9) -0.0194(8) N4 0.0435(8) 0.0547(9) 0.0762(10) 0.0080(8) -0.0081(8) -0.0069(6) K1 0.0378(2) 0.0692(3) 0.0320(2) -0.0059(2) -0.02048(19) 0.0033(2) O1 0.0423(5) 0.0564(6) 0.0330(5) -0.0090(4) -0.0227(4) 0.0050(5) O2 0.0334(5) 0.0650(7) 0.0320(5) -0.0110(4) -0.0165(4) 0.0019(4) O3 0.0387(5) 0.0573(6) 0.0300(5) -0.0072(4) -0.0190(4) 0.0071(4) C10 0.0444(8) 0.0618(10) 0.0359(7) -0.0080(7) -0.0197(6) 0.0116(7) C11 0.0334(7) 0.0728(11) 0.0349(7) -0.0095(7) -0.0171(6) 0.0069(7) C12 0.0392(8) 0.0536(9) 0.0371(7) -0.0047(6) -0.0228(6) -0.0014(6) C13 0.0410(8) 0.0531(9) 0.0325(7) -0.0058(6) -0.0228(6) 0.0020(6) C14 0.0378(7) 0.0544(9) 0.0295(6) -0.0080(6) -0.0172(6) 0.0008(6) C15 0.0442(8) 0.0521(9) 0.0395(7) -0.0053(6) -0.0215(7) -0.0040(7) C16 0.0572(10) 0.0609(10) 0.0483(9) -0.0186(8) -0.0296(8) 0.0090(8) C17 0.0385(8) 0.0987(14) 0.0386(8) -0.0153(9) -0.0136(7) 0.0051(9) C18 0.0478(9) 0.0959(14) 0.0380(8) -0.0014(9) -0.0157(7) -0.0115(9) C19 0.0524(9) 0.0623(10) 0.0390(8) -0.0008(7) -0.0241(7) -0.0098(8) O21 0.0610(18) 0.118(3) 0.0511(15) 0.0297(17) -0.0205(13) -0.0327(18) C21 0.096(4) 0.107(6) 0.065(3) 0.005(3) -0.045(3) -0.046(4) C22 0.050(2) 0.127(5) 0.068(3) 0.003(3) -0.0235(19) -0.015(2) C23 0.056(2) 0.062(3) 0.049(2) 0.0092(17) -0.0155(17) -0.020(2) C24 0.050(2) 0.108(6) 0.064(3) 0.024(3) -0.018(2) -0.019(3) O31 0.174(7) 0.096(4) 0.178(7) 0.066(4) -0.134(6) -0.083(5) C31 0.133(8) 0.094(7) 0.111(9) 0.015(5) -0.096(7) -0.030(5) C32 0.098(5) 0.089(5) 0.159(8) 0.039(5) -0.084(6) -0.048(4) C33 0.129(8) 0.085(6) 0.178(10) 0.054(6) -0.102(8) -0.055(5) C34 0.139(11) 0.071(6) 0.112(8) 0.024(4) -0.097(8) -0.039(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.3564(18) . ? C1 C2 1.388(2) . ? C1 C3 1.435(2) . ? C2 N1 1.3620(18) 2_657 ? C2 C4 1.430(2) . ? C3 N3 1.142(2) . ? C4 N4 1.146(2) . ? N1 C2 1.3620(18) 2_657 ? K1 O31 2.548(5) . ? K1 O31 2.548(5) 2_666 ? K1 O3 2.7014(11) . ? K1 O3 2.7015(11) 2_666 ? K1 O2 2.7520(10) 2_666 ? K1 O2 2.7520(10) . ? K1 O1 2.9075(11) . ? K1 O1 2.9075(11) 2_666 ? K1 O21 2.942(6) 2_666 ? K1 O21 2.942(6) . ? K1 C31 3.492(12) . ? K1 C31 3.492(12) 2_666 ? O1 C10 1.4228(16) . ? O1 C15 1.4370(17) 2_666 ? O2 C12 1.4183(16) . ? O2 C11 1.4240(16) . ? O3 C13 1.4237(15) . ? O3 C14 1.4262(16) . ? C10 C11 1.481(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.492(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C19 1.497(2) . ? C14 C15 1.5194(19) . ? C14 H14A 1.0000 . ? C15 O1 1.4370(17) 2_666 ? C15 C16 1.527(2) . ? C15 H15A 1.0000 . ? C16 C17 1.485(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.525(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.531(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? O21 C24 1.397(8) . ? O21 C21 1.430(8) . ? C21 C22 1.494(9) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.508(6) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.481(8) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? O31 C31 1.279(12) . ? O31 C34 1.457(10) . ? C31 C32 1.519(13) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.464(9) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.364(13) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 124.04(13) . . ? N1 C1 C3 116.18(13) . . ? C2 C1 C3 119.77(14) . . ? N1 C2 C1 123.35(13) 2_657 . ? N1 C2 C4 116.39(13) 2_657 . ? C1 C2 C4 120.25(13) . . ? N3 C3 C1 179.5(2) . . ? N4 C4 C2 179.31(17) . . ? C1 N1 C2 112.61(12) . 2_657 ? O31 K1 O31 180.000(2) . 2_666 ? O31 K1 O3 90.68(19) . . ? O31 K1 O3 89.32(19) 2_666 . ? O31 K1 O3 89.32(19) . 2_666 ? O31 K1 O3 90.68(19) 2_666 2_666 ? O3 K1 O3 180.0 . 2_666 ? O31 K1 O2 84.91(16) . 2_666 ? O31 K1 O2 95.09(16) 2_666 2_666 ? O3 K1 O2 119.20(3) . 2_666 ? O3 K1 O2 60.80(3) 2_666 2_666 ? O31 K1 O2 95.09(16) . . ? O31 K1 O2 84.91(16) 2_666 . ? O3 K1 O2 60.80(3) . . ? O3 K1 O2 119.20(3) 2_666 . ? O2 K1 O2 180.00(4) 2_666 . ? O31 K1 O1 87.9(3) . . ? O31 K1 O1 92.1(3) 2_666 . ? O3 K1 O1 121.44(3) . . ? O3 K1 O1 58.56(3) 2_666 . ? O2 K1 O1 118.94(3) 2_666 . ? O2 K1 O1 61.06(3) . . ? O31 K1 O1 92.1(3) . 2_666 ? O31 K1 O1 87.9(3) 2_666 2_666 ? O3 K1 O1 58.56(3) . 2_666 ? O3 K1 O1 121.44(3) 2_666 2_666 ? O2 K1 O1 61.06(3) 2_666 2_666 ? O2 K1 O1 118.94(3) . 2_666 ? O1 K1 O1 180.00(4) . 2_666 ? O31 K1 O21 161.5(3) . 2_666 ? O31 K1 O21 18.5(3) 2_666 2_666 ? O3 K1 O21 99.39(7) . 2_666 ? O3 K1 O21 80.61(7) 2_666 2_666 ? O2 K1 O21 103.27(7) 2_666 2_666 ? O2 K1 O21 76.73(7) . 2_666 ? O1 K1 O21 73.58(7) . 2_666 ? O1 K1 O21 106.42(7) 2_666 2_666 ? O31 K1 O21 18.5(3) . . ? O31 K1 O21 161.5(3) 2_666 . ? O3 K1 O21 80.61(7) . . ? O3 K1 O21 99.39(7) 2_666 . ? O2 K1 O21 76.73(7) 2_666 . ? O2 K1 O21 103.27(7) . . ? O1 K1 O21 106.42(7) . . ? O1 K1 O21 73.58(7) 2_666 . ? O21 K1 O21 180.0 2_666 . ? O31 K1 C31 16.65(19) . . ? O31 K1 C31 163.35(19) 2_666 . ? O3 K1 C31 80.22(18) . . ? O3 K1 C31 99.78(18) 2_666 . ? O2 K1 C31 101.31(16) 2_666 . ? O2 K1 C31 78.69(16) . . ? O1 K1 C31 82.6(2) . . ? O1 K1 C31 97.4(2) 2_666 . ? O21 K1 C31 151.81(18) 2_666 . ? O21 K1 C31 28.19(18) . . ? O31 K1 C31 163.35(19) . 2_666 ? O31 K1 C31 16.65(19) 2_666 2_666 ? O3 K1 C31 99.78(18) . 2_666 ? O3 K1 C31 80.22(18) 2_666 2_666 ? O2 K1 C31 78.69(16) 2_666 2_666 ? O2 K1 C31 101.31(16) . 2_666 ? O1 K1 C31 97.4(2) . 2_666 ? O1 K1 C31 82.6(2) 2_666 2_666 ? O21 K1 C31 28.19(18) 2_666 2_666 ? O21 K1 C31 151.81(18) . 2_666 ? C31 K1 C31 179.999(1) . 2_666 ? C10 O1 C15 114.36(11) . 2_666 ? C10 O1 K1 108.85(7) . . ? C15 O1 K1 110.67(8) 2_666 . ? C12 O2 C11 112.20(11) . . ? C12 O2 K1 111.68(8) . . ? C11 O2 K1 114.85(7) . . ? C13 O3 C14 114.13(9) . . ? C13 O3 K1 119.28(7) . . ? C14 O3 K1 123.70(7) . . ? O1 C10 C11 109.38(12) . . ? O1 C10 H10A 109.8 . . ? C11 C10 H10A 109.8 . . ? O1 C10 H10B 109.8 . . ? C11 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? O2 C11 C10 109.27(12) . . ? O2 C11 H11A 109.8 . . ? C10 C11 H11A 109.8 . . ? O2 C11 H11B 109.8 . . ? C10 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? O2 C12 C13 108.76(11) . . ? O2 C12 K1 46.40(6) . . ? C13 C12 K1 81.22(7) . . ? O2 C12 H12A 109.9 . . ? C13 C12 H12A 109.9 . . ? K1 C12 H12A 86.1 . . ? O2 C12 H12B 109.9 . . ? C13 C12 H12B 109.9 . . ? K1 C12 H12B 156.2 . . ? H12A C12 H12B 108.3 . . ? O3 C13 C12 108.40(10) . . ? O3 C13 H13A 110.0 . . ? C12 C13 H13A 110.0 . . ? O3 C13 H13B 110.0 . . ? C12 C13 H13B 110.0 . . ? H13A C13 H13B 108.4 . . ? O3 C14 C19 113.97(13) . . ? O3 C14 C15 107.39(10) . . ? C19 C14 C15 111.63(12) . . ? O3 C14 H14A 107.9 . . ? C19 C14 H14A 107.9 . . ? C15 C14 H14A 107.9 . . ? O1 C15 C14 106.67(12) 2_666 . ? O1 C15 C16 112.52(12) 2_666 . ? C14 C15 C16 108.57(11) . . ? O1 C15 H15A 109.7 2_666 . ? C14 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? C17 C16 C15 112.20(14) . . ? C17 C16 H16A 109.2 . . ? C15 C16 H16A 109.2 . . ? C17 C16 H16B 109.2 . . ? C15 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C16 C17 C18 110.82(14) . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 C19 111.21(13) . . ? C17 C18 H18A 109.4 . . ? C19 C18 H18A 109.4 . . ? C17 C18 H18B 109.4 . . ? C19 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? C14 C19 C18 110.66(14) . . ? C14 C19 H19A 109.5 . . ? C18 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? C24 O21 C21 106.2(5) . . ? C24 O21 K1 117.6(4) . . ? C21 O21 K1 115.4(4) . . ? O21 C21 C22 102.3(4) . . ? O21 C21 H21A 111.3 . . ? C22 C21 H21A 111.3 . . ? O21 C21 H21B 111.3 . . ? C22 C21 H21B 111.3 . . ? H21A C21 H21B 109.2 . . ? C21 C22 C23 104.0(4) . . ? C21 C22 H22A 110.9 . . ? C23 C22 H22A 110.9 . . ? C21 C22 H22B 110.9 . . ? C23 C22 H22B 110.9 . . ? H22A C22 H22B 109.0 . . ? C24 C23 C22 104.3(4) . . ? C24 C23 H23A 110.9 . . ? C22 C23 H23A 110.9 . . ? C24 C23 H23B 110.9 . . ? C22 C23 H23B 110.9 . . ? H23A C23 H23B 108.9 . . ? O21 C24 C23 106.8(4) . . ? O21 C24 H24A 110.4 . . ? C23 C24 H24A 110.4 . . ? O21 C24 H24B 110.4 . . ? C23 C24 H24B 110.4 . . ? H24A C24 H24B 108.6 . . ? C31 O31 C34 109.8(7) . . ? C31 O31 K1 128.5(6) . . ? C34 O31 K1 121.0(5) . . ? O31 C31 C32 107.9(7) . . ? O31 C31 K1 34.8(4) . . ? C32 C31 K1 141.7(6) . . ? O31 C31 H31A 110.1 . . ? C32 C31 H31A 110.1 . . ? K1 C31 H31A 96.3 . . ? O31 C31 H31B 110.1 . . ? C32 C31 H31B 110.1 . . ? K1 C31 H31B 85.8 . . ? H31A C31 H31B 108.4 . . ? C33 C32 C31 102.6(6) . . ? C33 C32 H32A 111.2 . . ? C31 C32 H32A 111.2 . . ? C33 C32 H32B 111.2 . . ? C31 C32 H32B 111.2 . . ? H32A C32 H32B 109.2 . . ? C34 C33 C32 108.5(6) . . ? C34 C33 H33A 110.0 . . ? C32 C33 H33A 110.0 . . ? C34 C33 H33B 110.0 . . ? C32 C33 H33B 110.0 . . ? H33A C33 H33B 108.4 . . ? C33 C34 O31 107.2(7) . . ? C33 C34 K1 144.6(6) . . ? O31 C34 K1 38.2(4) . . ? C33 C34 H34A 110.3 . . ? O31 C34 H34A 110.3 . . ? K1 C34 H34A 94.0 . . ? C33 C34 H34B 110.3 . . ? O31 C34 H34B 110.3 . . ? K1 C34 H34B 84.3 . . ? H34A C34 H34B 108.5 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.321 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.048 # Attachment 'TCP-TTF.cif' data_ros68 _database_code_depnum_ccdc_archive 'CCDC 703969' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 S4, C8 N6' _chemical_formula_sum 'C14 H4 N6 S4' _chemical_formula_weight 384.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0656(8) _cell_length_b 7.8452(11) _cell_length_c 8.6868(12) _cell_angle_alpha 86.475(2) _cell_angle_beta 75.290(2) _cell_angle_gamma 75.507(2) _cell_volume 387.10(9) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 194 _exptl_absorpt_coefficient_mu 0.622 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8353 _exptl_absorpt_correction_T_max 0.8856 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5845 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2273 _reflns_number_gt 2124 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.0992P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2273 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0820 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.23225(5) 0.67748(4) 0.17849(3) 0.02863(10) Uani 1 1 d . . . S2 S 0.72541(5) 0.49274(4) 0.16315(4) 0.03332(10) Uani 1 1 d . . . C1 C 0.5702(3) 0.62401(19) 0.32903(14) 0.0357(3) Uani 1 1 d . . . H1 H 0.6416 0.6352 0.4122 0.043 Uiso 1 1 calc R . . C2 C 0.3487(3) 0.70798(18) 0.33557(14) 0.0349(3) Uani 1 1 d . . . H2 H 0.2569 0.7821 0.4230 0.042 Uiso 1 1 calc R . . C3 C 0.49128(19) 0.53507(14) 0.07153(12) 0.0237(2) Uani 1 1 d . . . C4 C 0.2516(2) 0.21116(15) 0.26323(13) 0.0268(2) Uani 1 1 d . . . C5 C 0.37776(19) 0.10284(14) 0.12497(12) 0.0240(2) Uani 1 1 d . . . C6 C 0.38967(19) -0.00557(14) -0.11281(12) 0.0242(2) Uani 1 1 d . . . C7 C 0.2759(2) -0.01359(15) -0.23909(13) 0.0276(2) Uani 1 1 d . . . N1 N 0.1598(2) 0.29575(16) 0.37481(13) 0.0358(2) Uani 1 1 d . . . N2 N 0.26543(16) 0.09725(12) 0.01200(10) 0.0255(2) Uani 1 1 d . . . N3 N 0.1906(2) -0.02078(16) -0.34076(13) 0.0375(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.02798(15) 0.02801(16) 0.02813(15) -0.00728(10) -0.00385(11) -0.00495(11) S2 0.02918(16) 0.04362(19) 0.03045(16) -0.00453(12) -0.01294(12) -0.00804(12) C1 0.0462(7) 0.0473(7) 0.0214(5) -0.0015(5) -0.0107(5) -0.0227(6) C2 0.0466(7) 0.0388(6) 0.0209(5) -0.0074(4) -0.0011(5) -0.0190(5) C3 0.0240(4) 0.0254(5) 0.0229(5) -0.0030(4) -0.0060(4) -0.0072(4) C4 0.0288(5) 0.0293(5) 0.0235(5) -0.0031(4) -0.0071(4) -0.0077(4) C5 0.0288(5) 0.0239(5) 0.0196(4) -0.0021(4) -0.0046(4) -0.0078(4) C6 0.0290(5) 0.0251(5) 0.0203(4) -0.0012(4) -0.0075(4) -0.0083(4) C7 0.0304(5) 0.0279(5) 0.0245(5) -0.0049(4) -0.0076(4) -0.0052(4) N1 0.0375(6) 0.0404(6) 0.0288(5) -0.0086(4) -0.0045(4) -0.0098(5) N2 0.0290(5) 0.0261(5) 0.0218(4) -0.0025(3) -0.0066(4) -0.0067(4) N3 0.0427(6) 0.0392(6) 0.0342(5) -0.0068(4) -0.0167(5) -0.0074(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.7413(13) . ? S1 C3 1.7571(11) . ? S2 C1 1.7411(14) . ? S2 C3 1.7510(11) . ? C1 C2 1.329(2) . ? C1 H1 0.9500 . ? C2 H2 0.9500 . ? C3 C3 1.359(2) 2_665 ? C4 N1 1.1446(16) . ? C4 C5 1.4434(15) . ? C5 N2 1.3375(14) . ? C5 C6 1.4068(15) 2_655 ? C6 N2 1.3351(14) . ? C6 C5 1.4067(15) 2_655 ? C6 C7 1.4483(15) . ? C7 N3 1.1421(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C3 94.85(6) . . ? C1 S2 C3 94.94(6) . . ? C2 C1 S2 117.85(9) . . ? C2 C1 H1 121.1 . . ? S2 C1 H1 121.1 . . ? C1 C2 S1 117.74(9) . . ? C1 C2 H2 121.1 . . ? S1 C2 H2 121.1 . . ? C3 C3 S2 122.79(12) 2_665 . ? C3 C3 S1 122.58(12) 2_665 . ? S2 C3 S1 114.62(6) . . ? N1 C4 C5 177.23(13) . . ? N2 C5 C6 121.98(9) . 2_655 ? N2 C5 C4 117.86(10) . . ? C6 C5 C4 120.15(10) 2_655 . ? N2 C6 C5 122.60(10) . 2_655 ? N2 C6 C7 117.28(10) . . ? C5 C6 C7 120.12(10) 2_655 . ? N3 C7 C6 178.63(13) . . ? C6 N2 C5 115.42(9) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.280 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.136 # Attachment 'TCP-bp.cif' data_kimusx _database_code_depnum_ccdc_archive 'CCDC 703970' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8, C8 N6' _chemical_formula_sum 'C20 H8 N6' _chemical_formula_weight 332.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.6134(4) _cell_length_b 6.9065(3) _cell_length_c 13.2991(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.2680(10) _cell_angle_gamma 90.00 _cell_volume 791.13(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_method 'omega-scan, full sphere' _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3439 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 35.77 _reflns_number_total 3439 _reflns_number_gt 2926 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT & SADABS (Bruker, 2003)' _computing_structure_solution 'SHELXTL (Bruker, 2003)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'XP (Bruker, 1999)' _computing_publication_material 'SHELXL, XCIF (Bruker, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0820P)^2^+0.0544P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3439 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1236 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1A C 0.85974(7) 0.44449(9) 0.03031(5) 0.01761(12) Uani 1 1 d . . . C2A C 0.90211(7) 0.44270(10) -0.07187(5) 0.01784(12) Uani 1 1 d . . . N3A N 1.04218(7) 0.49851(9) -0.10227(4) 0.01852(12) Uani 1 1 d . . . C3A C 0.70606(8) 0.38902(10) 0.06156(5) 0.02107(14) Uani 1 1 d . . . C4A C 0.79463(8) 0.37646(11) -0.14805(5) 0.02246(14) Uani 1 1 d . . . N1 N 0.58248(8) 0.34886(11) 0.08631(5) 0.02753(15) Uani 1 1 d . . . N2 N 0.70770(9) 0.31922(13) -0.20691(5) 0.03278(17) Uani 1 1 d . . . C1 C 0.03470(7) 0.00622(9) -0.07442(5) 0.01661(12) Uani 1 1 d . . . C2 C 0.10652(8) 0.02708(11) -0.16558(5) 0.02019(13) Uani 1 1 d . . . C3 C 0.26272(8) 0.09169(11) -0.16091(5) 0.02216(14) Uani 1 1 d . . . C4 C 0.33728(8) 0.13020(11) -0.07055(5) 0.02142(14) Uani 1 1 d . . . C5 C 0.26220(7) 0.10836(10) 0.02359(5) 0.01951(13) Uani 1 1 d . . . C6 C 0.11105(7) 0.04687(9) 0.01841(5) 0.01627(12) Uani 1 1 d . . . H2 H 0.0619(15) 0.0008(18) -0.2273(9) 0.034(3) Uiso 1 1 d . . . H3 H 0.3254(13) 0.1025(19) -0.2272(9) 0.035(3) Uiso 1 1 d . . . H4 H 0.4480(13) 0.1759(19) -0.0712(8) 0.032(3) Uiso 1 1 d . . . H5 H 0.3173(13) 0.1380(18) 0.0844(9) 0.035(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.0176(2) 0.0159(3) 0.0193(3) 0.0004(2) 0.00281(19) -0.00045(19) C2A 0.0186(3) 0.0167(3) 0.0182(2) 0.00016(19) 0.00094(19) -0.00011(19) N3A 0.0190(2) 0.0176(3) 0.0190(2) 0.00039(18) 0.00205(18) -0.00046(18) C3A 0.0205(3) 0.0213(3) 0.0214(3) -0.0013(2) 0.0026(2) -0.0024(2) C4A 0.0214(3) 0.0247(3) 0.0212(3) 0.0008(2) 0.0004(2) -0.0003(2) N1 0.0221(3) 0.0323(3) 0.0281(3) -0.0037(2) 0.0038(2) -0.0061(2) N2 0.0287(3) 0.0394(4) 0.0301(3) -0.0017(3) -0.0066(3) -0.0018(3) C1 0.0170(2) 0.0162(3) 0.0167(2) 0.00043(19) 0.00141(18) -0.00083(19) C2 0.0213(3) 0.0223(3) 0.0170(2) -0.0004(2) 0.0025(2) -0.0020(2) C3 0.0216(3) 0.0239(3) 0.0211(3) 0.0003(2) 0.0064(2) -0.0025(2) C4 0.0176(3) 0.0217(3) 0.0250(3) -0.0005(2) 0.0038(2) -0.0026(2) C5 0.0163(3) 0.0209(3) 0.0213(3) -0.0008(2) 0.0005(2) -0.0023(2) C6 0.0160(2) 0.0161(3) 0.0167(2) 0.00010(19) 0.00138(18) -0.00109(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A N3A 1.3330(9) 3_765 ? C1A C2A 1.4087(9) . ? C1A C3A 1.4412(9) . ? C2A N3A 1.3312(8) . ? C2A C4A 1.4436(10) . ? N3A C1A 1.3330(9) 3_765 ? C3A N1 1.1496(9) . ? C4A N2 1.1507(10) . ? C1 C2 1.3711(9) . ? C1 C6 1.4240(9) . ? C1 C6 1.5080(8) 3 ? C2 C3 1.4186(10) . ? C2 H2 0.923(12) . ? C3 C4 1.3856(10) . ? C3 H3 1.038(12) . ? C4 C5 1.4198(9) . ? C4 H4 1.005(11) . ? C5 C6 1.3709(9) . ? C5 H5 0.958(12) . ? C6 C1 1.5080(8) 3 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3A C1A C2A 121.93(6) 3_765 . ? N3A C1A C3A 116.83(6) 3_765 . ? C2A C1A C3A 121.22(6) . . ? N3A C2A C1A 121.98(6) . . ? N3A C2A C4A 117.24(6) . . ? C1A C2A C4A 120.77(6) . . ? C2A N3A C1A 116.09(6) . 3_765 ? N1 C3A C1A 178.53(8) . . ? N2 C4A C2A 177.96(8) . . ? C2 C1 C6 122.51(6) . . ? C2 C1 C6 147.38(6) . 3 ? C6 C1 C6 90.10(5) . 3 ? C1 C2 C3 115.22(6) . . ? C1 C2 H2 125.3(8) . . ? C3 C2 H2 119.5(8) . . ? C4 C3 C2 122.27(6) . . ? C4 C3 H3 118.8(7) . . ? C2 C3 H3 118.9(7) . . ? C3 C4 C5 122.22(6) . . ? C3 C4 H4 119.3(6) . . ? C5 C4 H4 118.5(6) . . ? C6 C5 C4 115.15(6) . . ? C6 C5 H5 125.1(7) . . ? C4 C5 H5 119.7(7) . . ? C5 C6 C1 122.63(6) . . ? C5 C6 C1 147.48(6) . 3 ? C1 C6 C1 89.90(5) . 3 ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.468 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.067 # Attachment 'TCP-pi-dimer.cif' data_TCP_Dimer _database_code_depnum_ccdc_archive 'CCDC 703971' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H24 N4, 2(C8 N6), 2(C2 H3 N' _chemical_formula_sum 'C30 H30 N18' _chemical_formula_weight 642.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' _symmetry_space_group_name_hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.971(15) _cell_length_b 13.39(2) _cell_length_c 33.07(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6631(16) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour dark _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2688 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9745 _exptl_absorpt_correction_T_max 0.9863 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 43697 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 46 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 30.56 _reflns_number_total 9903 _reflns_number_gt 5031 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9903 _refine_ls_number_parameters 443 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1425 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.1916 _refine_ls_wR_factor_gt 0.1532 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.67404(10) 0.22661(12) 0.09880(5) 0.0332(4) Uani 1 1 d . . . N2 N 0.83075(10) 0.22947(12) 0.14965(5) 0.0336(4) Uani 1 1 d . . . N3 N 0.72890(13) 0.20595(16) 0.24214(6) 0.0547(5) Uani 1 1 d . . . N4 N 0.51377(12) 0.19532(14) 0.17090(5) 0.0463(5) Uani 1 1 d . . . N5 N 0.77602(13) 0.25330(16) 0.00630(5) 0.0528(5) Uani 1 1 d . . . N6 N 0.99131(12) 0.25395(14) 0.07772(6) 0.0478(5) Uani 1 1 d . . . C1 C 0.75943(13) 0.23729(15) 0.08394(6) 0.0339(4) Uani 1 1 d . . . C2 C 0.83376(12) 0.23682(14) 0.10940(6) 0.0312(4) Uani 1 1 d . . . C3 C 0.74512(13) 0.22208(15) 0.16448(6) 0.0330(4) Uani 1 1 d . . . C4 C 0.67059(13) 0.21907(14) 0.13884(6) 0.0318(4) Uani 1 1 d . . . C5 C 0.76875(14) 0.24587(16) 0.04086(6) 0.0387(5) Uani 1 1 d . . . C6 C 0.92215(14) 0.24595(15) 0.09210(6) 0.0345(5) Uani 1 1 d . . . C7 C 0.73590(13) 0.21291(16) 0.20758(6) 0.0375(5) Uani 1 1 d . . . C8 C 0.58241(14) 0.20597(15) 0.15622(6) 0.0345(4) Uani 1 1 d . . . N7 N 0.84170(10) 0.46992(12) 0.12767(4) 0.0306(4) Uani 1 1 d . . . N8 N 0.64925(10) 0.46455(13) 0.12498(4) 0.0371(4) Uani 1 1 d . . . N9 N 0.61856(13) 0.48523(18) 0.02307(5) 0.0641(6) Uani 1 1 d . . . N10 N 0.88147(12) 0.49228(16) 0.02577(5) 0.0496(5) Uani 1 1 d . . . N11 N 0.87177(12) 0.44976(17) 0.22952(5) 0.0542(5) Uani 1 1 d . . . N12 N 0.60791(12) 0.44485(18) 0.22662(5) 0.0582(6) Uani 1 1 d . . . C9 C 0.69969(12) 0.47216(16) 0.09218(5) 0.0340(5) Uani 1 1 d . . . C10 C 0.79346(12) 0.47318(15) 0.09221(5) 0.0303(4) Uani 1 1 d . . . C11 C 0.79103(12) 0.46212(15) 0.16063(5) 0.0309(4) Uani 1 1 d . . . C12 C 0.69713(12) 0.45749(16) 0.16036(5) 0.0346(5) Uani 1 1 d . . . C13 C 0.65329(13) 0.47962(18) 0.05353(6) 0.0436(5) Uani 1 1 d . . . C14 C 0.84294(12) 0.48410(16) 0.05545(6) 0.0354(5) Uani 1 1 d . . . C15 C 0.83738(13) 0.45551(17) 0.19905(6) 0.0367(5) Uani 1 1 d . . . C16 C 0.64750(13) 0.45074(19) 0.19693(6) 0.0424(5) Uani 1 1 d . . . C17 C 0.19865(12) 0.47515(13) 0.12473(5) 0.0248(4) Uani 1 1 d . . . C18 C 0.29969(11) 0.47515(13) 0.12501(5) 0.0238(4) Uani 1 1 d . . . C19 C 0.06862(12) 0.48616(16) 0.07998(6) 0.0359(5) Uani 1 1 d . . . H19A H 0.0245 0.4338 0.0854 0.054 Uiso 1 1 calc R . . H19B H 0.0672 0.5035 0.0512 0.054 Uiso 1 1 calc R . . H19C H 0.0545 0.5454 0.0961 0.054 Uiso 1 1 calc R . . C20 C 0.20328(13) 0.39130(15) 0.05896(5) 0.0352(5) Uani 1 1 d . . . H20A H 0.2196 0.4356 0.0365 0.053 Uiso 1 1 calc R . . H20B H 0.1628 0.3392 0.0491 0.053 Uiso 1 1 calc R . . H20C H 0.2573 0.3603 0.0701 0.053 Uiso 1 1 calc R . . C21 C 0.06688(12) 0.46375(16) 0.16844(6) 0.0350(5) Uani 1 1 d . . . H21A H 0.0226 0.5156 0.1625 0.053 Uiso 1 1 calc R . . H21B H 0.0645 0.4469 0.1973 0.053 Uiso 1 1 calc R . . H21C H 0.0538 0.4041 0.1523 0.053 Uiso 1 1 calc R . . C22 C 0.20088(13) 0.55889(15) 0.19028(5) 0.0343(4) Uani 1 1 d . . . H22A H 0.2169 0.5144 0.2127 0.051 Uiso 1 1 calc R . . H22B H 0.1601 0.6107 0.2001 0.051 Uiso 1 1 calc R . . H22C H 0.2550 0.5902 0.1795 0.051 Uiso 1 1 calc R . . C23 C 0.29508(13) 0.33077(15) 0.17003(6) 0.0385(5) Uani 1 1 d . . . H23A H 0.2856 0.3431 0.1989 0.058 Uiso 1 1 calc R . . H23B H 0.3327 0.2714 0.1666 0.058 Uiso 1 1 calc R . . H23C H 0.2373 0.3199 0.1568 0.058 Uiso 1 1 calc R . . C24 C 0.43136(12) 0.43331(16) 0.16617(5) 0.0342(5) Uani 1 1 d . . . H24A H 0.4716 0.3865 0.1525 0.051 Uiso 1 1 calc R . . H24B H 0.4339 0.4220 0.1954 0.051 Uiso 1 1 calc R . . H24C H 0.4498 0.5020 0.1602 0.051 Uiso 1 1 calc R . . C25 C 0.43205(12) 0.51562(15) 0.08377(6) 0.0345(5) Uani 1 1 d . . . H25A H 0.4730 0.5618 0.0974 0.052 Uiso 1 1 calc R . . H25B H 0.4346 0.5268 0.0545 0.052 Uiso 1 1 calc R . . H25C H 0.4497 0.4467 0.0897 0.052 Uiso 1 1 calc R . . C26 C 0.29634(13) 0.61946(15) 0.07973(6) 0.0382(5) Uani 1 1 d . . . H26A H 0.2864 0.6063 0.0509 0.057 Uiso 1 1 calc R . . H26B H 0.3344 0.6785 0.0828 0.057 Uiso 1 1 calc R . . H26C H 0.2389 0.6314 0.0931 0.057 Uiso 1 1 calc R . . N13 N 0.15838(9) 0.44964(11) 0.09079(4) 0.0272(3) Uani 1 1 d . . . N14 N 0.15689(9) 0.50091(12) 0.15825(4) 0.0276(3) Uani 1 1 d . . . N15 N 0.33949(9) 0.41746(11) 0.15176(4) 0.0261(3) Uani 1 1 d . . . N16 N 0.34024(9) 0.53295(11) 0.09829(4) 0.0273(3) Uani 1 1 d . . . C27 C 0.44464(15) 0.70055(16) 0.19196(7) 0.0423(5) Uani 1 1 d . . . C28 C 0.49949(18) 0.7060(2) 0.22799(7) 0.0656(8) Uani 1 1 d . . . H28A H 0.4803 0.7627 0.2446 0.098 Uiso 1 1 calc R . . H28B H 0.5622 0.7148 0.2202 0.098 Uiso 1 1 calc R . . H28C H 0.4931 0.6441 0.2435 0.098 Uiso 1 1 calc R . . C29 C 0.44554(15) 0.24614(16) 0.05879(7) 0.0429(5) Uani 1 1 d . . . C30 C 0.50088(18) 0.2350(2) 0.02305(7) 0.0636(7) Uani 1 1 d . . . H30A H 0.4789 0.1788 0.0068 0.095 Uiso 1 1 calc R . . H30B H 0.5628 0.2221 0.0312 0.095 Uiso 1 1 calc R . . H30C H 0.4983 0.2963 0.0070 0.095 Uiso 1 1 calc R . . N17 N 0.40126(14) 0.69639(15) 0.16395(6) 0.0523(5) Uani 1 1 d . . . N18 N 0.40218(14) 0.25413(15) 0.08669(6) 0.0535(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0299(9) 0.0377(10) 0.0320(9) -0.0013(7) -0.0024(7) -0.0017(7) N2 0.0310(9) 0.0361(9) 0.0339(9) 0.0017(7) -0.0024(7) 0.0024(7) N3 0.0536(13) 0.0755(15) 0.0352(10) 0.0099(9) -0.0054(9) -0.0021(10) N4 0.0387(11) 0.0507(12) 0.0494(11) 0.0058(9) 0.0006(9) -0.0008(9) N5 0.0553(13) 0.0699(14) 0.0331(10) -0.0052(9) -0.0045(9) -0.0058(10) N6 0.0395(11) 0.0524(13) 0.0515(12) 0.0041(9) 0.0025(9) 0.0051(9) C1 0.0338(11) 0.0369(11) 0.0311(10) -0.0027(8) -0.0031(8) 0.0019(9) C2 0.0308(10) 0.0303(11) 0.0324(10) -0.0006(8) -0.0027(8) 0.0027(8) C3 0.0345(11) 0.0341(11) 0.0306(10) 0.0018(8) -0.0030(8) 0.0007(9) C4 0.0323(11) 0.0298(10) 0.0334(10) 0.0003(8) -0.0041(8) -0.0001(8) C5 0.0353(12) 0.0461(13) 0.0346(11) -0.0059(9) -0.0038(9) -0.0019(9) C6 0.0339(11) 0.0343(11) 0.0353(11) 0.0013(8) -0.0030(9) 0.0055(9) C7 0.0345(12) 0.0431(12) 0.0349(11) 0.0029(9) -0.0041(9) -0.0026(9) C8 0.0345(11) 0.0345(11) 0.0344(10) 0.0010(8) -0.0047(9) 0.0006(9) N7 0.0220(8) 0.0427(10) 0.0270(8) -0.0003(7) -0.0016(6) -0.0001(7) N8 0.0243(8) 0.0586(12) 0.0285(8) -0.0063(7) -0.0009(7) 0.0026(7) N9 0.0413(12) 0.114(2) 0.0371(11) -0.0025(11) -0.0104(9) 0.0088(12) N10 0.0357(10) 0.0808(15) 0.0324(9) 0.0111(9) 0.0017(8) 0.0047(9) N11 0.0404(11) 0.0893(16) 0.0329(10) -0.0007(10) -0.0080(8) -0.0054(10) N12 0.0347(10) 0.1063(18) 0.0336(10) -0.0132(10) 0.0039(8) -0.0091(10) C9 0.0259(10) 0.0480(13) 0.0281(9) -0.0054(8) -0.0025(8) 0.0031(9) C10 0.0225(9) 0.0416(12) 0.0268(9) -0.0001(8) 0.0001(7) 0.0033(8) C11 0.0237(9) 0.0416(12) 0.0276(9) -0.0022(8) -0.0034(7) -0.0008(8) C12 0.0244(9) 0.0528(13) 0.0264(9) -0.0087(8) -0.0005(8) -0.0011(9) C13 0.0268(10) 0.0718(17) 0.0323(10) -0.0051(10) -0.0027(9) 0.0061(10) C14 0.0262(10) 0.0495(13) 0.0304(10) 0.0026(9) -0.0052(8) 0.0033(9) C15 0.0270(10) 0.0532(13) 0.0301(10) -0.0019(9) 0.0003(8) -0.0056(9) C16 0.0245(10) 0.0707(16) 0.0320(10) -0.0102(10) -0.0041(8) -0.0030(10) C17 0.0226(9) 0.0237(9) 0.0282(9) 0.0032(7) -0.0009(7) 0.0005(7) C18 0.0203(8) 0.0285(9) 0.0225(8) -0.0014(7) -0.0015(7) 0.0002(7) C19 0.0227(10) 0.0444(12) 0.0408(11) 0.0037(9) -0.0094(8) 0.0027(8) C20 0.0348(11) 0.0407(12) 0.0302(10) -0.0056(8) -0.0032(8) 0.0027(9) C21 0.0236(9) 0.0428(12) 0.0387(11) 0.0035(9) 0.0067(8) -0.0013(8) C22 0.0348(11) 0.0399(12) 0.0282(9) -0.0058(8) 0.0003(8) -0.0017(9) C23 0.0349(11) 0.0368(12) 0.0437(11) 0.0165(9) 0.0003(9) -0.0021(9) C24 0.0249(10) 0.0474(13) 0.0305(10) 0.0044(8) -0.0071(8) 0.0022(9) C25 0.0248(10) 0.0426(12) 0.0361(10) 0.0059(9) 0.0066(8) -0.0017(8) C26 0.0353(11) 0.0358(12) 0.0437(11) 0.0145(9) -0.0007(9) 0.0017(9) N13 0.0225(8) 0.0314(9) 0.0275(8) -0.0005(6) -0.0025(6) 0.0008(6) N14 0.0217(8) 0.0337(9) 0.0274(7) 0.0001(6) 0.0014(6) -0.0011(6) N15 0.0229(8) 0.0308(9) 0.0247(7) 0.0035(6) -0.0017(6) 0.0006(6) N16 0.0245(8) 0.0305(9) 0.0270(7) 0.0055(6) -0.0002(6) 0.0008(6) C27 0.0418(13) 0.0420(13) 0.0432(13) -0.0014(10) 0.0102(10) -0.0007(10) C28 0.0525(16) 0.095(2) 0.0493(15) -0.0010(14) 0.0001(12) 0.0009(14) C29 0.0417(13) 0.0408(13) 0.0463(13) -0.0044(10) -0.0095(11) 0.0001(10) C30 0.0529(16) 0.091(2) 0.0466(15) -0.0036(13) -0.0003(12) -0.0066(14) N17 0.0494(12) 0.0583(14) 0.0491(12) -0.0077(9) 0.0009(10) -0.0003(9) N18 0.0529(13) 0.0583(14) 0.0492(12) -0.0091(10) -0.0052(10) 0.0062(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C4 1.329(3) . ? N1 C1 1.377(3) . ? N2 C2 1.335(3) . ? N2 C3 1.376(3) . ? N3 C7 1.151(3) . ? N4 C8 1.145(3) . ? N5 C5 1.152(3) . ? N6 C6 1.144(3) . ? C1 C2 1.395(3) . ? C1 C5 1.436(3) . ? C2 C6 1.447(3) . ? C3 C4 1.402(3) . ? C3 C7 1.437(3) . ? C4 C8 1.451(3) . ? N7 C11 1.332(3) . ? N7 C10 1.378(3) . ? N8 C9 1.326(3) . ? N8 C12 1.375(3) . ? N9 C13 1.136(3) . ? N10 C14 1.144(3) . ? N11 C15 1.134(3) . ? N12 C16 1.150(3) . ? C9 C10 1.404(3) . ? C9 C13 1.458(3) . ? C10 C14 1.431(3) . ? C11 C12 1.407(3) . ? C11 C15 1.450(3) . ? C12 C16 1.422(3) . ? C17 N14 1.319(2) . ? C17 N13 1.319(2) . ? C17 C18 1.513(3) . ? C18 N15 1.317(2) . ? C18 N16 1.322(2) . ? C19 N13 1.474(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N13 1.473(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 N14 1.475(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 N14 1.469(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 N15 1.468(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 N15 1.471(3) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 N16 1.474(3) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N16 1.467(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 N17 1.133(3) . ? C27 C28 1.449(4) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 N18 1.133(3) . ? C29 C30 1.451(3) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C1 113.55(16) . . ? C2 N2 C3 113.08(16) . . ? N1 C1 C2 121.63(19) . . ? N1 C1 C5 116.91(17) . . ? C2 C1 C5 121.43(19) . . ? N2 C2 C1 125.09(18) . . ? N2 C2 C6 115.54(17) . . ? C1 C2 C6 119.36(19) . . ? N2 C3 C4 121.85(19) . . ? N2 C3 C7 116.70(17) . . ? C4 C3 C7 121.39(19) . . ? N1 C4 C3 124.72(18) . . ? N1 C4 C8 116.07(17) . . ? C3 C4 C8 119.21(19) . . ? N5 C5 C1 179.6(3) . . ? N6 C6 C2 178.6(2) . . ? N3 C7 C3 179.6(3) . . ? N4 C8 C4 178.2(2) . . ? C11 N7 C10 113.61(18) . . ? C9 N8 C12 113.87(19) . . ? N8 C9 C10 124.74(17) . . ? N8 C9 C13 116.82(19) . . ? C10 C9 C13 118.44(17) . . ? N7 C10 C9 121.62(16) . . ? N7 C10 C14 117.07(18) . . ? C9 C10 C14 121.20(16) . . ? N7 C11 C12 124.55(17) . . ? N7 C11 C15 116.69(18) . . ? C12 C11 C15 118.74(17) . . ? N8 C12 C11 121.53(17) . . ? N8 C12 C16 117.09(19) . . ? C11 C12 C16 121.29(17) . . ? N9 C13 C9 178.8(2) . . ? N10 C14 C10 179.0(2) . . ? N11 C15 C11 178.4(2) . . ? N12 C16 C12 179.5(3) . . ? N14 C17 N13 124.50(18) . . ? N14 C17 C18 117.97(15) . . ? N13 C17 C18 117.53(15) . . ? N15 C18 N16 125.78(18) . . ? N15 C18 C17 117.16(15) . . ? N16 C18 C17 117.07(15) . . ? N13 C19 H19A 109.5 . . ? N13 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N13 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N13 C20 H20A 109.5 . . ? N13 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N13 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N14 C21 H21A 109.5 . . ? N14 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N14 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N14 C22 H22A 109.5 . . ? N14 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N14 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N15 C23 H23A 109.5 . . ? N15 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N15 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N15 C24 H24A 109.5 . . ? N15 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N15 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N16 C25 H25A 109.5 . . ? N16 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N16 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N16 C26 H26A 109.5 . . ? N16 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N16 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C17 N13 C20 122.47(17) . . ? C17 N13 C19 122.49(16) . . ? C20 N13 C19 114.75(15) . . ? C17 N14 C22 122.13(17) . . ? C17 N14 C21 122.45(16) . . ? C22 N14 C21 115.03(15) . . ? C18 N15 C23 122.38(17) . . ? C18 N15 C24 123.78(16) . . ? C23 N15 C24 113.84(15) . . ? C18 N16 C26 122.44(17) . . ? C18 N16 C25 123.61(16) . . ? C26 N16 C25 113.94(15) . . ? N17 C27 C28 179.6(3) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N18 C29 C30 179.5(3) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.382 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.070 # Attachment 'TCP-pyr.cif' data_jlu35 _database_code_depnum_ccdc_archive 'CCDC 703972' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H10, C8 N6' _chemical_formula_sum 'C24 H10 N6' _chemical_formula_weight 382.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.747(3) _cell_length_b 6.940(2) _cell_length_c 15.327(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.356(7) _cell_angle_gamma 90.00 _cell_volume 901.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9825 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_method 'omega-scan, full sphere' _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8909 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0539 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 30.42 _reflns_number_total 2650 _reflns_number_gt 1664 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT & SADABS (Bruker, 2003)' _computing_structure_solution 'SHELXTL (Bruker, 2003)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'XP (Bruker, 1999)' _computing_publication_material 'SHELXL, XCIF (Bruker, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2650 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1407 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.43951(17) 0.6664(2) 0.08868(11) 0.0488(4) Uani 1 1 d . . . N2 N 0.06737(15) 0.53045(17) 0.09238(8) 0.0301(3) Uani 1 1 d . . . N3 N -0.24559(19) 0.4211(2) 0.17902(12) 0.0538(5) Uani 1 1 d . . . C1 C 0.31165(19) 0.6167(2) 0.06301(11) 0.0346(4) Uani 1 1 d . . . C2 C 0.14934(17) 0.5555(2) 0.03040(10) 0.0280(3) Uani 1 1 d . . . C3 C -0.08237(18) 0.4748(2) 0.06181(10) 0.0291(4) Uani 1 1 d . . . C4 C -0.17270(19) 0.4465(2) 0.12779(11) 0.0356(4) Uani 1 1 d . . . C5 C 0.1859(2) 0.0672(2) -0.10102(12) 0.0356(4) Uani 1 1 d . . . H5 H 0.2725 0.0991 -0.1254 0.043 Uiso 1 1 calc R . . C6 C 0.20424(18) 0.0790(2) -0.00549(11) 0.0300(4) Uani 1 1 d . . . C7 C 0.34525(18) 0.1355(2) 0.05441(12) 0.0378(4) Uani 1 1 d . . . H7 H 0.4336 0.1688 0.0318 0.045 Uiso 1 1 calc R . . C8 C 0.3578(2) 0.1434(2) 0.14597(13) 0.0429(4) Uani 1 1 d . . . H8 H 0.4547 0.1819 0.1856 0.052 Uiso 1 1 calc R . . C9 C 0.2309(2) 0.0959(2) 0.18081(12) 0.0412(4) Uani 1 1 d . . . H9 H 0.2418 0.1026 0.2440 0.049 Uiso 1 1 calc R . . C10 C 0.08659(19) 0.0380(2) 0.12404(11) 0.0311(4) Uani 1 1 d . . . C11 C -0.0482(2) -0.0117(2) 0.15693(11) 0.0355(4) Uani 1 1 d . . . H11 H -0.0404 -0.0054 0.2198 0.043 Uiso 1 1 calc R . . C12 C 0.07263(17) 0.02953(19) 0.02955(10) 0.0259(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0377(8) 0.0464(9) 0.0581(11) 0.0087(8) 0.0040(7) -0.0049(7) N2 0.0331(7) 0.0272(7) 0.0285(7) 0.0003(5) 0.0046(6) 0.0038(5) N3 0.0609(10) 0.0577(11) 0.0517(10) 0.0079(8) 0.0304(9) 0.0096(8) C1 0.0353(9) 0.0305(8) 0.0362(10) 0.0038(7) 0.0058(7) 0.0002(7) C2 0.0287(8) 0.0237(7) 0.0302(9) 0.0010(6) 0.0047(7) 0.0026(6) C3 0.0318(8) 0.0264(7) 0.0290(9) 0.0013(6) 0.0074(7) 0.0045(6) C4 0.0380(9) 0.0363(9) 0.0330(9) 0.0016(7) 0.0096(8) 0.0052(7) C5 0.0426(9) 0.0301(9) 0.0384(10) 0.0044(7) 0.0180(8) 0.0025(7) C6 0.0332(8) 0.0244(7) 0.0318(9) 0.0013(6) 0.0072(7) 0.0026(6) C7 0.0325(8) 0.0290(8) 0.0502(11) 0.0012(7) 0.0074(8) 0.0004(6) C8 0.0379(9) 0.0367(9) 0.0456(11) -0.0021(8) -0.0061(8) -0.0013(7) C9 0.0527(10) 0.0351(9) 0.0291(9) -0.0011(7) -0.0025(8) 0.0027(8) C10 0.0410(9) 0.0244(8) 0.0258(8) 0.0012(6) 0.0039(7) 0.0035(6) C11 0.0521(10) 0.0324(8) 0.0236(8) 0.0034(7) 0.0127(8) 0.0044(7) C12 0.0321(8) 0.0200(7) 0.0241(8) 0.0013(6) 0.0044(6) 0.0025(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.143(2) . ? N2 C3 1.3342(19) . ? N2 C2 1.3357(19) . ? N3 C4 1.141(2) . ? C1 C2 1.447(2) . ? C2 C3 1.405(2) 3_565 ? C3 C2 1.405(2) 3_565 ? C3 C4 1.443(2) . ? C5 C11 1.349(2) 3 ? C5 C6 1.435(2) . ? C5 H5 0.9500 . ? C6 C7 1.399(2) . ? C6 C12 1.428(2) . ? C7 C8 1.381(3) . ? C7 H7 0.9500 . ? C8 C9 1.385(3) . ? C8 H8 0.9500 . ? C9 C10 1.403(2) . ? C9 H9 0.9500 . ? C10 C12 1.424(2) . ? C10 C11 1.435(2) . ? C11 C5 1.349(2) 3 ? C11 H11 0.9500 . ? C12 C12 1.426(3) 3 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N2 C2 116.19(13) . . ? N1 C1 C2 179.47(18) . . ? N2 C2 C3 122.17(13) . 3_565 ? N2 C2 C1 116.50(14) . . ? C3 C2 C1 121.33(14) 3_565 . ? N2 C3 C2 121.64(14) . 3_565 ? N2 C3 C4 116.99(14) . . ? C2 C3 C4 121.37(14) 3_565 . ? N3 C4 C3 178.64(19) . . ? C11 C5 C6 121.37(15) 3 . ? C11 C5 H5 119.3 3 . ? C6 C5 H5 119.3 . . ? C7 C6 C12 118.85(14) . . ? C7 C6 C5 122.89(15) . . ? C12 C6 C5 118.26(14) . . ? C8 C7 C6 120.87(16) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 120.83(16) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C10 120.86(17) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C12 118.67(15) . . ? C9 C10 C11 122.87(15) . . ? C12 C10 C11 118.46(14) . . ? C5 C11 C10 121.83(15) 3 . ? C5 C11 H11 119.1 3 . ? C10 C11 H11 119.1 . . ? C10 C12 C12 119.76(17) . 3 ? C10 C12 C6 119.92(14) . . ? C12 C12 C6 120.32(17) 3 . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.355 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.056 # Attachment 'TCP-sigma-dimer.cif' data_ros8 _database_code_depnum_ccdc_archive 'CCDC 703973' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2,2-Cryptand potassium tetracyanopirazinide, tetrahydrofuran solvate ; _chemical_name_common '[Crypt K+] TCP- * THF' _chemical_melting_point ? _chemical_formula_moiety 'C18 H36 K N2 O6, 0.5(C16 N12), C4 H8 O' _chemical_formula_sum 'C30 H44 K N8 O7' _chemical_formula_weight 667.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.106(3) _cell_length_b 12.153(3) _cell_length_c 12.839(3) _cell_angle_alpha 97.619(5) _cell_angle_beta 99.310(5) _cell_angle_gamma 108.192(5) _cell_volume 1736.8(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 266 _cell_measurement_theta_min 1.81 _cell_measurement_theta_max 18.88 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 710 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 26532 _diffrn_reflns_av_R_equivalents 0.0729 _diffrn_reflns_av_sigmaI/netI 0.1201 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 30.55 _reflns_number_total 10228 _reflns_number_gt 5146 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.630 (BrukerAXS, 1997-2001)' _computing_cell_refinement 'SAINT V6.28 (BrukerAXS, 1997-2001)' _computing_data_reduction 'SAINT & SADABS V2.06 (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'XP V5.06 (BrukerAXS, 1997-99)' _computing_publication_material 'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0871P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10228 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1512 _refine_ls_R_factor_gt 0.0802 _refine_ls_wR_factor_ref 0.2000 _refine_ls_wR_factor_gt 0.1708 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group K1 K 0.87314(5) 0.71729(5) 0.55950(5) 0.02651(16) Uani 1 1 d . . . N1 N 0.6791(2) 0.6418(2) 0.35781(19) 0.0338(6) Uani 1 1 d . . . O3 O 0.91801(18) 0.81693(18) 0.37425(16) 0.0348(5) Uani 1 1 d . . . O1 O 0.65425(18) 0.74897(18) 0.56713(16) 0.0345(5) Uani 1 1 d . . . N4 N 0.5125(2) 0.8824(2) 0.1960(2) 0.0358(6) Uani 1 1 d . . . O2 O 0.84791(18) 0.8521(2) 0.74572(16) 0.0382(5) Uani 1 1 d . . . N3 N 0.3557(2) 0.9245(2) 0.0333(2) 0.0356(6) Uani 1 1 d . . . N6 N 0.3438(3) 0.8522(3) 0.3885(3) 0.0571(9) Uani 1 1 d . . . O6 O 0.9243(2) 0.5465(2) 0.66697(19) 0.0482(6) Uani 1 1 d . . . O5 O 0.7709(2) 0.47492(18) 0.46130(17) 0.0391(5) Uani 1 1 d . . . C3 C 0.6564(3) 0.8374(3) 0.6538(2) 0.0363(7) Uani 1 1 d . . . H3A H 0.5742 0.8283 0.6617 0.044 Uiso 1 1 calc R . . H3B H 0.6931 0.9170 0.6386 0.044 Uiso 1 1 calc R . . C20 C 0.3257(3) 0.8959(3) 0.1220(3) 0.0333(7) Uani 1 1 d . . . O4 O 1.10527(19) 0.85332(19) 0.55043(18) 0.0418(5) Uani 1 1 d . . . N8 N 0.5407(3) 1.1978(3) 0.1796(2) 0.0448(7) Uani 1 1 d . . . N2 N 1.0637(2) 0.7907(3) 0.7578(2) 0.0410(7) Uani 1 1 d . . . C25 C 0.3727(3) 0.8688(3) 0.3108(3) 0.0414(8) Uani 1 1 d . . . C24 C 0.1986(3) 0.8476(3) 0.1189(3) 0.0416(8) Uani 1 1 d . . . C7 C 0.7163(3) 0.7179(3) 0.2811(2) 0.0408(8) Uani 1 1 d . . . H7A H 0.7013 0.7926 0.3014 0.049 Uiso 1 1 calc R . . H7B H 0.6661 0.6785 0.2087 0.049 Uiso 1 1 calc R . . C22 C 0.5464(3) 0.9146(3) 0.1101(2) 0.0345(7) Uani 1 1 d . . . C23 C 0.4841(3) 0.9886(3) 0.0532(3) 0.0361(7) Uani 1 1 d . . . C8 C 0.8444(3) 0.7469(3) 0.2748(2) 0.0420(8) Uani 1 1 d . . . H8A H 0.8623 0.6731 0.2592 0.050 Uiso 1 1 calc R . . H8B H 0.8603 0.7905 0.2159 0.050 Uiso 1 1 calc R . . C26 C 0.6393(3) 0.8795(3) 0.0769(2) 0.0381(7) Uani 1 1 d . . . C9 C 1.0404(3) 0.8588(3) 0.3669(3) 0.0394(8) Uani 1 1 d . . . H9A H 1.0503 0.9098 0.3125 0.047 Uiso 1 1 calc R . . H9B H 1.0654 0.7910 0.3436 0.047 Uiso 1 1 calc R . . C2 C 0.5888(3) 0.7595(3) 0.4683(2) 0.0389(7) Uani 1 1 d . . . H2A H 0.6340 0.8315 0.4448 0.047 Uiso 1 1 calc R . . H2B H 0.5114 0.7657 0.4781 0.047 Uiso 1 1 calc R . . C1 C 0.5689(3) 0.6519(3) 0.3850(3) 0.0417(8) Uani 1 1 d . . . H1A H 0.5280 0.5806 0.4118 0.050 Uiso 1 1 calc R . . H1B H 0.5156 0.6541 0.3187 0.050 Uiso 1 1 calc R . . C21 C 0.4079(3) 0.8936(3) 0.2136(3) 0.0354(7) Uani 1 1 d . . . C27 C 0.5183(3) 1.1106(3) 0.1245(2) 0.0336(7) Uani 1 1 d . . . N7 N 0.7124(3) 0.8486(3) 0.0493(2) 0.0540(8) Uani 1 1 d . . . C4 C 0.7264(3) 0.8243(3) 0.7546(2) 0.0387(7) Uani 1 1 d . . . H4A H 0.7206 0.8783 0.8167 0.046 Uiso 1 1 calc R . . H4B H 0.6947 0.7423 0.7660 0.046 Uiso 1 1 calc R . . C13 C 0.6606(3) 0.5184(3) 0.3110(2) 0.0431(8) Uani 1 1 d . . . H13A H 0.7256 0.5171 0.2734 0.052 Uiso 1 1 calc R . . H13B H 0.5848 0.4864 0.2566 0.052 Uiso 1 1 calc R . . C16 C 0.8900(4) 0.4301(3) 0.6032(3) 0.0569(10) Uani 1 1 d . . . H16A H 0.8912 0.3726 0.6509 0.068 Uiso 1 1 calc R . . H16B H 0.9472 0.4279 0.5566 0.068 Uiso 1 1 calc R . . C14 C 0.6571(3) 0.4399(3) 0.3908(3) 0.0450(8) Uani 1 1 d . . . H14A H 0.5965 0.4448 0.4329 0.054 Uiso 1 1 calc R . . H14B H 0.6347 0.3571 0.3530 0.054 Uiso 1 1 calc R . . C10 C 1.1161(3) 0.9267(3) 0.4727(3) 0.0425(8) Uani 1 1 d . . . H10A H 1.2002 0.9576 0.4666 0.051 Uiso 1 1 calc R . . H10B H 1.0914 0.9948 0.4958 0.051 Uiso 1 1 calc R . . N5 N 0.0996(3) 0.8115(3) 0.1167(3) 0.0687(10) Uani 1 1 d . . . C6 C 1.0492(3) 0.8880(3) 0.8296(3) 0.0496(9) Uani 1 1 d . . . H6A H 1.0730 0.9604 0.7992 0.059 Uiso 1 1 calc R . . H6B H 1.1035 0.9031 0.9004 0.059 Uiso 1 1 calc R . . C15 C 0.7686(4) 0.3979(3) 0.5359(3) 0.0528(10) Uani 1 1 d . . . H15A H 0.7417 0.3150 0.4967 0.063 Uiso 1 1 calc R . . H15B H 0.7122 0.4049 0.5821 0.063 Uiso 1 1 calc R . . C5 C 0.9241(3) 0.8638(4) 0.8460(3) 0.0484(9) Uani 1 1 d . . . H5A H 0.8979 0.7903 0.8744 0.058 Uiso 1 1 calc R . . H5B H 0.9211 0.9296 0.8986 0.058 Uiso 1 1 calc R . . C11 C 1.1870(3) 0.9123(4) 0.6490(3) 0.0580(11) Uani 1 1 d . . . H11A H 1.1688 0.9824 0.6790 0.070 Uiso 1 1 calc R . . H11B H 1.2688 0.9396 0.6364 0.070 Uiso 1 1 calc R . . C17 C 1.0355(4) 0.5771(4) 0.7386(3) 0.0579(11) Uani 1 1 d . . . H17A H 1.0994 0.5857 0.6977 0.070 Uiso 1 1 calc R . . H17B H 1.0352 0.5141 0.7804 0.070 Uiso 1 1 calc R . . C18 C 1.0583(4) 0.6915(4) 0.8137(3) 0.0552(10) Uani 1 1 d . . . H18A H 0.9942 0.6813 0.8545 0.066 Uiso 1 1 calc R . . H18B H 1.1345 0.7110 0.8660 0.066 Uiso 1 1 calc R . . C12 C 1.1793(3) 0.8310(4) 0.7277(3) 0.0581(11) Uani 1 1 d . . . H12A H 1.1969 0.7611 0.6962 0.070 Uiso 1 1 calc R . . H12B H 1.2415 0.8720 0.7936 0.070 Uiso 1 1 calc R . . O7 O 0.2220(4) 0.5024(4) -0.0731(3) 0.1118(13) Uani 1 1 d . . . C33 C 0.3254(6) 0.5880(6) -0.0189(4) 0.127(3) Uani 1 1 d . . . H33A H 0.3138 0.6654 -0.0065 0.152 Uiso 1 1 calc R . . H33B H 0.3881 0.5939 -0.0608 0.152 Uiso 1 1 calc R . . C32 C 0.3590(8) 0.5559(9) 0.0813(6) 0.196(4) Uani 1 1 d . . . H32A H 0.4218 0.5203 0.0774 0.235 Uiso 1 1 calc R . . H32B H 0.3912 0.6270 0.1393 0.235 Uiso 1 1 calc R . . C30 C 0.1756(7) 0.4453(9) 0.0054(5) 0.201(5) Uani 1 1 d . . . H30A H 0.1487 0.3587 -0.0203 0.242 Uiso 1 1 calc R . . H30B H 0.1058 0.4665 0.0185 0.242 Uiso 1 1 calc R . . C31 C 0.2631(10) 0.4777(9) 0.1033(7) 0.249(7) Uani 1 1 d . . . H31A H 0.2358 0.5144 0.1631 0.299 Uiso 1 1 calc R . . H31B H 0.2812 0.4080 0.1227 0.299 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 K1 0.0211(3) 0.0279(3) 0.0298(3) 0.0056(2) 0.0047(2) 0.0078(2) N1 0.0298(14) 0.0401(15) 0.0284(13) 0.0055(11) 0.0035(11) 0.0095(12) O3 0.0303(12) 0.0386(12) 0.0364(12) 0.0079(9) 0.0143(10) 0.0091(10) O1 0.0282(11) 0.0450(12) 0.0323(11) 0.0047(9) 0.0038(9) 0.0181(10) N4 0.0328(15) 0.0404(15) 0.0368(14) 0.0115(12) 0.0086(12) 0.0140(12) O2 0.0277(12) 0.0533(14) 0.0306(11) 0.0017(10) 0.0046(9) 0.0131(10) N3 0.0192(13) 0.0442(15) 0.0417(15) 0.0124(12) 0.0073(11) 0.0063(11) N6 0.062(2) 0.078(2) 0.058(2) 0.0377(18) 0.0284(18) 0.0427(19) O6 0.0510(15) 0.0445(14) 0.0494(14) 0.0103(11) -0.0063(12) 0.0246(12) O5 0.0442(14) 0.0308(11) 0.0379(12) 0.0087(9) 0.0063(11) 0.0071(10) C3 0.0304(17) 0.0431(18) 0.0413(18) 0.0068(14) 0.0145(14) 0.0179(15) C20 0.0239(15) 0.0338(16) 0.0414(18) 0.0099(13) 0.0086(14) 0.0067(13) O4 0.0265(12) 0.0440(13) 0.0463(13) 0.0050(11) 0.0082(10) 0.0016(10) N8 0.0376(16) 0.0451(17) 0.0425(16) -0.0022(13) 0.0050(13) 0.0078(14) N2 0.0296(15) 0.0550(18) 0.0351(15) 0.0047(13) -0.0017(12) 0.0159(13) C25 0.041(2) 0.051(2) 0.048(2) 0.0251(17) 0.0157(17) 0.0275(17) C24 0.0302(18) 0.055(2) 0.0333(18) 0.0031(15) 0.0118(14) 0.0050(16) C7 0.0393(19) 0.053(2) 0.0283(16) 0.0124(15) 0.0019(14) 0.0135(16) C22 0.0245(16) 0.0417(18) 0.0363(17) 0.0130(14) 0.0038(13) 0.0091(14) C23 0.0237(16) 0.0450(19) 0.0387(17) 0.0130(14) 0.0054(14) 0.0094(14) C8 0.048(2) 0.052(2) 0.0303(17) 0.0138(15) 0.0132(16) 0.0183(17) C26 0.0320(18) 0.050(2) 0.0313(17) 0.0127(14) 0.0047(14) 0.0125(16) C9 0.0372(19) 0.0373(18) 0.057(2) 0.0212(16) 0.0301(17) 0.0164(15) C2 0.0269(16) 0.051(2) 0.0411(18) 0.0107(15) 0.0050(14) 0.0175(15) C1 0.0275(17) 0.055(2) 0.0357(18) 0.0062(16) -0.0012(14) 0.0096(16) C21 0.0298(17) 0.0398(17) 0.0413(18) 0.0156(14) 0.0113(14) 0.0136(14) C27 0.0208(15) 0.0425(18) 0.0314(16) -0.0019(14) 0.0005(13) 0.0088(14) N7 0.0479(19) 0.078(2) 0.0502(18) 0.0226(17) 0.0158(16) 0.0348(18) C4 0.0338(18) 0.0484(19) 0.0360(17) 0.0037(14) 0.0141(15) 0.0153(16) C13 0.041(2) 0.047(2) 0.0284(16) -0.0032(14) -0.0019(15) 0.0062(16) C16 0.074(3) 0.041(2) 0.064(3) 0.0201(18) 0.008(2) 0.030(2) C14 0.046(2) 0.0307(17) 0.044(2) -0.0021(14) 0.0049(17) 0.0001(16) C10 0.0288(17) 0.0340(17) 0.067(2) 0.0098(16) 0.0238(17) 0.0067(14) N5 0.0327(18) 0.107(3) 0.052(2) 0.0057(19) 0.0178(16) 0.0027(19) C6 0.037(2) 0.059(2) 0.0379(19) -0.0054(16) -0.0093(16) 0.0111(18) C15 0.071(3) 0.0287(17) 0.056(2) 0.0130(16) 0.012(2) 0.0120(18) C5 0.045(2) 0.066(2) 0.0304(17) 0.0001(16) 0.0012(16) 0.0223(19) C11 0.0250(18) 0.066(3) 0.059(2) -0.006(2) 0.0028(17) -0.0068(18) C17 0.060(3) 0.069(3) 0.052(2) 0.016(2) -0.005(2) 0.040(2) C18 0.052(2) 0.077(3) 0.0374(19) 0.0089(19) -0.0084(17) 0.033(2) C12 0.0235(18) 0.086(3) 0.052(2) 0.002(2) -0.0038(16) 0.0106(19) O7 0.100(3) 0.125(3) 0.081(2) 0.023(2) -0.001(2) 0.006(3) C33 0.138(6) 0.101(4) 0.073(4) -0.005(3) 0.003(4) -0.036(4) C32 0.147(8) 0.240(10) 0.113(6) 0.063(7) -0.066(5) -0.020(7) C30 0.136(7) 0.284(11) 0.072(4) 0.063(6) 0.005(4) -0.087(7) C31 0.235(12) 0.222(10) 0.140(7) 0.106(7) -0.033(8) -0.123(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag K1 O6 2.808(2) . ? K1 O1 2.809(2) . ? K1 O4 2.811(2) . ? K1 O2 2.829(2) . ? K1 O5 2.834(2) . ? K1 O3 2.862(2) . ? K1 N2 2.968(3) . ? K1 N1 3.020(3) . ? N1 C7 1.468(4) . ? N1 C1 1.469(4) . ? N1 C13 1.471(4) . ? O3 C8 1.421(4) . ? O3 C9 1.432(4) . ? O1 C2 1.426(3) . ? O1 C3 1.432(3) . ? N4 C22 1.303(4) . ? N4 C21 1.365(4) . ? O2 C5 1.419(4) . ? O2 C4 1.430(4) . ? N3 C20 1.309(4) . ? N3 C23 1.466(4) . ? N6 C25 1.132(4) . ? O6 C17 1.412(4) . ? O6 C16 1.434(4) . ? O5 C15 1.423(4) . ? O5 C14 1.424(4) . ? C3 C4 1.483(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C20 C21 1.421(4) . ? C20 C24 1.457(4) . ? O4 C11 1.416(4) . ? O4 C10 1.419(4) . ? N8 C27 1.121(4) . ? N2 C12 1.465(4) . ? N2 C18 1.472(5) . ? N2 C6 1.474(4) . ? C25 C21 1.422(4) . ? C24 N5 1.134(4) . ? C7 C8 1.497(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C22 C26 1.426(4) . ? C22 C23 1.528(4) . ? C23 C23 1.515(6) 2_675 ? C23 C27 1.530(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C26 N7 1.151(4) . ? C9 C10 1.482(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C2 C1 1.504(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C13 C14 1.487(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C16 C15 1.483(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C6 C5 1.505(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C11 C12 1.497(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C17 C18 1.502(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? O7 C33 1.359(6) . ? O7 C30 1.392(7) . ? C33 C32 1.427(9) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C32 C31 1.349(10) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C30 C31 1.426(10) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 K1 O1 116.82(7) . . ? O6 K1 O4 99.49(7) . . ? O1 K1 O4 138.38(7) . . ? O6 K1 O2 94.48(7) . . ? O1 K1 O2 60.17(6) . . ? O4 K1 O2 99.40(7) . . ? O6 K1 O5 60.06(7) . . ? O1 K1 O5 94.94(7) . . ? O4 K1 O5 121.78(7) . . ? O2 K1 O5 133.19(7) . . ? O6 K1 O3 139.40(7) . . ? O1 K1 O3 98.53(6) . . ? O4 K1 O3 59.40(6) . . ? O2 K1 O3 121.46(7) . . ? O5 K1 O3 99.68(6) . . ? O6 K1 N2 59.90(8) . . ? O1 K1 N2 119.82(7) . . ? O4 K1 N2 61.12(7) . . ? O2 K1 N2 60.42(7) . . ? O5 K1 N2 119.18(7) . . ? O3 K1 N2 119.70(7) . . ? O6 K1 N1 119.90(7) . . ? O1 K1 N1 60.24(6) . . ? O4 K1 N1 118.98(7) . . ? O2 K1 N1 119.68(7) . . ? O5 K1 N1 60.63(7) . . ? O3 K1 N1 60.43(7) . . ? N2 K1 N1 179.81(7) . . ? C7 N1 C1 109.7(2) . . ? C7 N1 C13 109.9(2) . . ? C1 N1 C13 110.3(3) . . ? C7 N1 K1 109.29(18) . . ? C1 N1 K1 109.54(17) . . ? C13 N1 K1 108.16(17) . . ? C8 O3 C9 111.0(2) . . ? C8 O3 K1 114.83(17) . . ? C9 O3 K1 115.33(17) . . ? C2 O1 C3 110.7(2) . . ? C2 O1 K1 116.00(16) . . ? C3 O1 K1 115.71(16) . . ? C22 N4 C21 117.2(3) . . ? C5 O2 C4 111.7(2) . . ? C5 O2 K1 119.09(18) . . ? C4 O2 K1 112.44(17) . . ? C20 N3 C23 110.3(2) . . ? C17 O6 C16 111.5(3) . . ? C17 O6 K1 119.0(2) . . ? C16 O6 K1 115.94(18) . . ? C15 O5 C14 109.8(3) . . ? C15 O5 K1 113.40(18) . . ? C14 O5 K1 116.16(17) . . ? O1 C3 C4 108.9(2) . . ? O1 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? O1 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? N3 C20 C21 123.9(3) . . ? N3 C20 C24 116.5(3) . . ? C21 C20 C24 119.0(3) . . ? C11 O4 C10 111.0(3) . . ? C11 O4 K1 117.76(19) . . ? C10 O4 K1 116.78(18) . . ? C12 N2 C18 108.9(3) . . ? C12 N2 C6 109.8(3) . . ? C18 N2 C6 109.6(3) . . ? C12 N2 K1 108.62(19) . . ? C18 N2 K1 111.0(2) . . ? C6 N2 K1 108.87(18) . . ? N6 C25 C21 177.9(3) . . ? N5 C24 C20 179.1(4) . . ? N1 C7 C8 114.6(3) . . ? N1 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? N1 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? N4 C22 C26 117.9(3) . . ? N4 C22 C23 117.1(3) . . ? C26 C22 C23 124.9(3) . . ? N3 C23 C23 108.3(3) . 2_675 ? N3 C23 C22 106.9(2) . . ? C23 C23 C22 115.0(3) 2_675 . ? N3 C23 C27 111.5(2) . . ? C23 C23 C27 105.7(3) 2_675 . ? C22 C23 C27 109.5(3) . . ? O3 C8 C7 109.5(3) . . ? O3 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? O3 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? N7 C26 C22 178.5(4) . . ? O3 C9 C10 110.1(2) . . ? O3 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? O3 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.2 . . ? O1 C2 C1 108.4(2) . . ? O1 C2 H2A 110.0 . . ? C1 C2 H2A 110.0 . . ? O1 C2 H2B 110.0 . . ? C1 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? N1 C1 C2 113.7(3) . . ? N1 C1 H1A 108.8 . . ? C2 C1 H1A 108.8 . . ? N1 C1 H1B 108.8 . . ? C2 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? N4 C21 C20 116.6(3) . . ? N4 C21 C25 118.9(3) . . ? C20 C21 C25 122.0(3) . . ? N8 C27 C23 177.1(3) . . ? O2 C4 C3 108.6(2) . . ? O2 C4 H4A 110.0 . . ? C3 C4 H4A 110.0 . . ? O2 C4 H4B 110.0 . . ? C3 C4 H4B 110.0 . . ? H4A C4 H4B 108.4 . . ? N1 C13 C14 114.2(3) . . ? N1 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? N1 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? O6 C16 C15 109.6(3) . . ? O6 C16 H16A 109.7 . . ? C15 C16 H16A 109.7 . . ? O6 C16 H16B 109.7 . . ? C15 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? O5 C14 C13 109.7(3) . . ? O5 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? O5 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? O4 C10 C9 110.0(3) . . ? O4 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? O4 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? N2 C6 C5 113.7(3) . . ? N2 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? N2 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? O5 C15 C16 109.0(3) . . ? O5 C15 H15A 109.9 . . ? C16 C15 H15A 109.9 . . ? O5 C15 H15B 109.9 . . ? C16 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? O2 C5 C6 108.7(3) . . ? O2 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? O2 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? O4 C11 C12 110.2(3) . . ? O4 C11 H11A 109.6 . . ? C12 C11 H11A 109.6 . . ? O4 C11 H11B 109.6 . . ? C12 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? O6 C17 C18 109.0(3) . . ? O6 C17 H17A 109.9 . . ? C18 C17 H17A 109.9 . . ? O6 C17 H17B 109.9 . . ? C18 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? N2 C18 C17 113.2(3) . . ? N2 C18 H18A 108.9 . . ? C17 C18 H18A 108.9 . . ? N2 C18 H18B 108.9 . . ? C17 C18 H18B 108.9 . . ? H18A C18 H18B 107.8 . . ? N2 C12 C11 114.4(3) . . ? N2 C12 H12A 108.6 . . ? C11 C12 H12A 108.6 . . ? N2 C12 H12B 108.6 . . ? C11 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C33 O7 C30 104.9(5) . . ? O7 C33 C32 107.1(6) . . ? O7 C33 H33A 110.3 . . ? C32 C33 H33A 110.3 . . ? O7 C33 H33B 110.3 . . ? C32 C33 H33B 110.3 . . ? H33A C33 H33B 108.5 . . ? C31 C32 C33 109.5(7) . . ? C31 C32 H32A 109.8 . . ? C33 C32 H32A 109.8 . . ? C31 C32 H32B 109.8 . . ? C33 C32 H32B 109.8 . . ? H32A C32 H32B 108.2 . . ? O7 C30 C31 110.7(6) . . ? O7 C30 H30A 109.5 . . ? C31 C30 H30A 109.5 . . ? O7 C30 H30B 109.5 . . ? C31 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? C32 C31 C30 103.8(6) . . ? C32 C31 H31A 111.0 . . ? C30 C31 H31A 111.0 . . ? C32 C31 H31B 111.0 . . ? C30 C31 H31B 111.0 . . ? H31A C31 H31B 109.0 . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.805 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.083 # Attachment 'TCP.cif' data_TCP _database_code_depnum_ccdc_archive 'CCDC 703974' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 N6' _chemical_formula_sum 'C8 N6' _chemical_formula_weight 180.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' _symmetry_space_group_name_hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.090(2) _cell_length_b 12.141(3) _cell_length_c 13.850(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1696.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9767 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11774 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 30.55 _reflns_number_total 2529 _reflns_number_gt 1931 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens . _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2529 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.275 _refine_ls_restrained_S_all 1.275 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.11187(8) 0.97500(7) 0.10610(6) 0.0258(2) Uani 1 1 d . . . N2 N 0.24246(9) 0.77273(7) 0.13800(7) 0.0271(2) Uani 1 1 d . . . N3 N 0.10284(11) 0.70024(9) 0.35392(8) 0.0419(3) Uani 1 1 d . . . N4 N -0.07326(11) 0.98847(10) 0.31311(7) 0.0415(3) Uani 1 1 d . . . N5 N 0.25304(11) 1.04938(9) -0.10849(8) 0.0419(3) Uani 1 1 d . . . N6 N 0.44066(12) 0.76564(10) -0.06232(8) 0.0495(3) Uani 1 1 d . . . C1 C 0.19895(10) 0.93384(9) 0.04331(7) 0.0251(2) Uani 1 1 d . . . C2 C 0.26459(10) 0.83355(9) 0.05975(8) 0.0261(2) Uani 1 1 d . . . C3 C 0.15520(10) 0.81384(8) 0.20057(7) 0.0249(2) Uani 1 1 d . . . C4 C 0.09150(9) 0.91517(8) 0.18511(7) 0.0241(2) Uani 1 1 d . . . C5 C 0.22705(11) 0.99874(10) -0.04151(8) 0.0306(3) Uani 1 1 d . . . C6 C 0.36268(11) 0.79412(9) -0.00833(9) 0.0326(3) Uani 1 1 d . . . C7 C 0.12688(11) 0.74912(9) 0.28583(8) 0.0298(3) Uani 1 1 d . . . C8 C -0.00089(10) 0.95774(9) 0.25583(8) 0.0284(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0235(4) 0.0277(4) 0.0262(5) 0.0002(4) -0.0003(3) -0.0003(3) N2 0.0252(4) 0.0276(5) 0.0287(5) -0.0020(4) -0.0027(4) -0.0005(3) N3 0.0529(7) 0.0362(6) 0.0366(6) 0.0067(5) 0.0000(5) -0.0024(5) N4 0.0399(6) 0.0439(6) 0.0409(6) 0.0049(5) 0.0136(5) 0.0044(5) N5 0.0463(6) 0.0409(6) 0.0384(6) 0.0058(5) 0.0079(4) -0.0035(5) N6 0.0435(7) 0.0515(7) 0.0535(7) -0.0081(6) 0.0142(5) 0.0078(5) C1 0.0234(5) 0.0278(5) 0.0242(5) -0.0016(4) 0.0002(4) -0.0023(4) C2 0.0228(5) 0.0287(5) 0.0269(6) -0.0035(4) -0.0009(4) -0.0001(4) C3 0.0238(5) 0.0267(5) 0.0243(5) -0.0008(4) -0.0037(4) -0.0034(4) C4 0.0212(5) 0.0277(5) 0.0235(5) -0.0009(4) -0.0011(4) -0.0028(4) C5 0.0299(6) 0.0310(6) 0.0309(6) -0.0009(5) 0.0033(5) 0.0004(4) C6 0.0313(6) 0.0326(6) 0.0340(6) -0.0030(5) 0.0023(5) 0.0021(5) C7 0.0329(6) 0.0265(5) 0.0300(6) -0.0001(4) -0.0021(5) -0.0001(4) C8 0.0272(5) 0.0298(5) 0.0282(5) 0.0040(4) 0.0017(4) 0.0006(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C4 1.3294(13) . ? N1 C1 1.3334(13) . ? N2 C2 1.3303(14) . ? N2 C3 1.3325(14) . ? N3 C7 1.1403(15) . ? N4 C8 1.1410(14) . ? N5 C5 1.1434(15) . ? N6 C6 1.1393(15) . ? C1 C2 1.4047(15) . ? C1 C5 1.4425(15) . ? C2 C6 1.4484(15) . ? C3 C4 1.4044(14) . ? C3 C7 1.4469(15) . ? C4 C8 1.4476(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C1 115.72(9) . . ? C2 N2 C3 115.64(9) . . ? N1 C1 C2 121.99(10) . . ? N1 C1 C5 117.13(10) . . ? C2 C1 C5 120.85(10) . . ? N2 C2 C1 122.29(9) . . ? N2 C2 C6 117.49(10) . . ? C1 C2 C6 120.21(10) . . ? N2 C3 C4 122.10(10) . . ? N2 C3 C7 117.25(9) . . ? C4 C3 C7 120.65(10) . . ? N1 C4 C3 122.23(9) . . ? N1 C4 C8 117.48(9) . . ? C3 C4 C8 120.29(9) . . ? N5 C5 C1 178.05(13) . . ? N6 C6 C2 178.36(13) . . ? N3 C7 C3 178.31(12) . . ? N4 C8 C4 177.95(12) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.390 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.060